Lithium Hydroxide → HCID 21876358, compound

HRID 858507Notes

Reaction equation

HRID 858507 reaction equation
C([O:4][C:5]([CH3:17])([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=O)C.[Li+].[OH-]>CO>[CH3:17][C:5]([OH:4])([CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67099422HCID 67099422, compound

Product 1

HCID 21876358HCID 21876358, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1,1-dimethyl-2-(4-nitrophenyl)ethyl acetate (52 mmol) in MeOH (50 ml) was added 4N—LiOH (40 ml) and the mixture was stirred at 50° C. for 2 h. After the solvent was removed, this mixture was diluted with water and extracted with EtOAc (4×50 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated. This crude was purified by SiO2 column chromatography developing with hexane/ethyl acetate (5/1) to give the title compound as yellow oil (3.3 g, 33%).

Workup

  1. customAfter the solvent was removed
  2. additionthis mixture was diluted with water
  3. extractionextracted with EtOAc (4×50 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThis crude was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-0e647be8271e43c4b0f716f36d3a92b8
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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